Does anyone know why AA doesn't allow you to upgrade 3 people in a reservation? Earlier this year wife, 3yos and myself flew to Curacao. No one could upgrade us on the way over there but the CSR at the counter in Curacao was able to upgrade all 3 of us using the 500 mile tickets on the first leg of the return trip.

I've always heard the excuse that the system won't allow it but that one time it was proof that it is possible if they wanted to.